Phosphoric Acid → HCID 57896664, Verbindung

HRID 2421886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421886
[NH:1]1[CH2:6][CH2:5][O:4][C:3]2[N:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:2]1=2.C(N(CC)CC)C.[N:22]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.OP(O)(O)=O>ClCCCl.CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:25]1[CH2:26][CH2:27][N:22]([S:28]([N:1]2[CH2:6][CH2:5][O:4][C:3]3[N:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:2]2=3)(=[O:30])=[O:29])[CH2:23][CH2:24]1

Komponenten

8

Edukt 4

HCID 1004Phosphoric AcidHCID 8471TriethylamineHCID 12798265Morpholine-4-sulfonyl chlorideHCID 57896765methyl 2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

Produkt 1

HCID 57896664HCID 57896664, VerbindungAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate (97 mg, 0.50 mmol) was suspended in 4 mL of DCE and sequentially treated with DMAP (61 mg, 0.50 mmol) and triethylamine (0.077 mL, 0.55 mmol). Morpholine-4-sulfonyl chloride (102 mg, 0.55 mmol) was added and the mixture was stirred at ambient temperature for 2 hours and then heated to 50° C. for 2 days. The mixture was cooled to ambient temperature and diluted with 10 mL of DCM and the whole solution poured into 15 mL of 1M aqueous H3PO4. The layers were separated and the aqueous layer was extracted with 10 mL of DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by normal phase flash chromatography (gradient elution 50% to 100% EtOAc/Hexanes) to provide 88 mg (51%) of the title compound as a thick tan oil. 1H NMR (CDCl3) δ 8.59 (d, 1H), 8.34 (d, 1H), 4.48 (m, 2H), 3.86 (s, 3H), 3.77 (m, 2H), 3.69 (m, 4H), 3.26 (m, 4H). LCMS (+ESI) m/z=344.1 [M+H]+.

Aufarbeitung

  1. temperatureheated to 50° C. for 2 days
  2. temperatureThe mixture was cooled to ambient temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 10 mL of DCM
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by normal phase flash chromatography (gradient elution 50% to 100% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b3ae56ec825d4d35ad584419d468eaff
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960377B2

Notizen zur Reaktion

Wird geladen…